Ortho alkylation of aromatic ketimine with functionalized alkene by Rh(l) catalyst

被引:99
作者
Lim, SG [1 ]
Ahn, JA [1 ]
Jun, CH [1 ]
机构
[1] Yonsei Univ, Dept Chem, CBMH, Seoul 120749, South Korea
关键词
D O I
10.1021/ol048095n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of the imine of aromatic ketones with functionalized alkenes was performed under a catalytic amount of (PPh3)(3)RhCl, and corresponding ortho-alkylated ketones were obtained after hydrolysis. A variety of functional groups in the alkene were tolerated in this ortho alkylation. This procedure expands the scope of ortho alkylation to the direct ortho functionalization of aromatic ketones.
引用
收藏
页码:4687 / 4690
页数:4
相关论文
共 32 条
[1]   Synthesis of a tricyclic mescaline analogue by catalytic C-H bond activation [J].
Ahrendt, KA ;
Bergman, RG ;
Ellman, JA .
ORGANIC LETTERS, 2003, 5 (08) :1301-1303
[2]   Convenient preparation of mononuclear and dinuclear ruthenium hydride complexes for catalytic application [J].
Busch, S ;
Leitner, W .
CHEMICAL COMMUNICATIONS, 1999, (22) :2305-2306
[3]  
Dyker G, 1999, ANGEW CHEM INT EDIT, V38, P1699, DOI 10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO
[4]  
2-6
[5]   Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].
Fagnou, K ;
Lautens, M .
CHEMICAL REVIEWS, 2003, 103 (01) :169-196
[6]   Transition metal catalysed alkylation of pyridines and indoles [J].
Grigg, R ;
Savic, V .
TETRAHEDRON LETTERS, 1997, 38 (32) :5737-5740
[7]   RUTHENIUM-CATALYZED REGIOSELECTIVE COPOLYMERIZATION OF ANTHRONE, FLUORENONE, OR XANTHONE WITH ALPHA, OMEGA-DIENES [J].
GUO, HJ ;
TAPSAK, MA ;
WEBER, WP .
POLYMER BULLETIN, 1995, 34 (01) :49-55
[8]   Ruthenium-catalysed ortho alkylation of hydroxyacetophenones; The functionalisation of ring C aromatic diterpenoids [J].
Harris, PWR ;
Woodgate, PD .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 530 (1-2) :211-223
[9]   DESIGN AND STUDY OF RH(III) CATALYSTS FOR THE SELECTIVE TAIL-TO-TAIL DIMERIZATION OF METHYL ACRYLATE [J].
HAUPTMAN, E ;
SABOETIENNE, S ;
WHITE, PS ;
BROOKHART, M ;
GARNER, JM ;
FAGAN, PJ ;
CALABRESE, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (18) :8038-8060
[10]  
Jun CH, 2000, ANGEW CHEM INT EDIT, V39, P3440, DOI 10.1002/1521-3773(20001002)39:19<3440::AID-ANIE3440>3.0.CO